5-[(二甲基氨基)磺酰基]-2-甲基-3-呋喃酸 | 306936-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 5-[(二甲基氨基)磺酰基]-2-甲基-3-呋喃酸
• 英文名称: 5-(Dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid
• CAS: 306936-39-0
• 化学式: C₈H₁₁NO₅S
• mdl: MFCD02180761
• 分子量: 233.245
• InChiKey: DUFCMRCMPHIFTR-UHFFFAOYSA-N

物化性质

• 熔点：
  169 °C
• 沸点：
  409.6±55.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  96.2
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2935009090
• 安全说明：
  S26,S36/37/39

反应信息

• 作为反应物：
  描述：

  5-[(二甲基氨基)磺酰基]-2-甲基-3-呋喃酸 、 苯胺 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 5-[(dimethylamino)sulfonyl]-2-methyl-N-phenyl-3-furamide 、 5-Methyl-4-(3-phenyl-ureido)-furan-2-sulfonic acid dimethylamide
  参考文献：
  名称：

  Discovery of potent, selective sulfonylfuran urea endothelial lipase inhibitors

  摘要：

  Endothelial lipase (EL) activity has been implicated in HDL catabolism, vascular inflammation, and atherogenesis, and inhibitors are therefore expected to be useful for the treatment of cardiovascular disease. Sulfonylfuran urea 1 was identified in a high-throughput screening campaign as a potent and non-selective EL inhibitor. A lead optimization effort was undertaken to improve potency and selectivity, and modifications leading to improved LPL selectivity were identified. Radiolabeling studies were undertaken to establish the mechanism of action for these inhibitors, which were ultimately demonstrated to be irreversible inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.033
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 5-[(二甲基氨基)磺酰基]-2-甲基-3-呋喃酸
  参考文献：
  名称：

  Discovery of potent, selective sulfonylfuran urea endothelial lipase inhibitors

  摘要：

  Endothelial lipase (EL) activity has been implicated in HDL catabolism, vascular inflammation, and atherogenesis, and inhibitors are therefore expected to be useful for the treatment of cardiovascular disease. Sulfonylfuran urea 1 was identified in a high-throughput screening campaign as a potent and non-selective EL inhibitor. A lead optimization effort was undertaken to improve potency and selectivity, and modifications leading to improved LPL selectivity were identified. Radiolabeling studies were undertaken to establish the mechanism of action for these inhibitors, which were ultimately demonstrated to be irreversible inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.033

文献信息

• [EN] CATHEPSIN S INHIBITORS<br/>[FR] INHIBITEURS DE CATHEPSINE S
  申请人：MEDIVIR UK LTD

  公开号：WO2006064286A1

  公开（公告）日：2006-06-22

  [EN] Compounds of the formula (I) where R¹ is C₁-C₄ straight or branched alkyl, optionally substituted with up to three substituents selected from halo and hydroxy; R² is halo, hydroxy, methyloxy, or C₁-C₂ alkyl, which alkyl is optionally substituted with up to three halogens or an hydroxy or a methyloxy; D is - C₃-C₇ alkylene-, thereby defining a cycloalkyl ring; E is -C(=O)-, -S(=O)_m-, -NRdS(=O)_m-, -NRaC(=O)-, -OC(=O)-, R³ is an optionally substituted carbocyclic or heterocyclic ring R¹⁰ is H, ORc, SRc or together with the gem H is =O or (ORc)₂; Ra is independently selected from H, C₁-C₄ alkyl; have utility in the inhibition of cathepsin S and are thus useful pharmaceuticals against disorders such as autoimmune disorders and chronic pain.
  [FR] La présente invention décrit des composés de formule (I) où R¹ est un groupement alkyle linéaire ou ramifié en C₁-C₄, éventuellement substitué par jusqu'à trois substituants sélectionnés parmi les halogènes et le groupement hydroxy ; R² représente un atome d'halogène, un groupement hydroxy, un groupement méthyloxy, ou un groupement alkyle en C₁-C₂, ledit alkyle étant éventuellement substitué par jusqu'à trois atomes d'halogène, un groupement hydroxy ou un groupement méthyloxy ; D représente un groupement alkylène en C₃-C₇, délimitant un cycle cycloalkyle ; E représente un groupement -C(=O)-, -S(=O)_m-, -NRdS(=O)_m-, -NRaC(=O)- ou -OC(=O)-, R³ représente un groupement carbocyclique ou hétérocyclique éventuellement substitué, R¹⁰ représente H, ORc, SRc ou représente =O or (ORc)₂ avec le gem H ; Ra est sélectionné de façon indépendante parmi H et et les groupements alkyle en d-C₄. Lesdits composés peuvent être employés en tant qu'inhibiteurs de la cathepsine S et présentent donc une utilité pharmaceutique contre les troubles tels que les troubles auto-immuns et les douleurs chroniques.
• Discovery of potent, selective sulfonylfuran urea endothelial lipase inhibitors
  作者：Krista B. Goodman、Michael J. Bury、Mui Cheung、Maria A. Cichy-Knight、Sarah E. Dowdell、Allison K. Dunn、Dennis Lee、Jeffrey A. Lieby、Michael L. Moore、Daryl A. Scherzer、Deyou Sha、Dominic P. Suarez、Dennis J. Murphy、Mark R. Harpel、Eric S. Manas、Dean E. McNulty、Roland S. Annan、Rosalie E. Matico、Benjamin K. Schwartz、John J. Trill、Thomas D. Sweitzer、Da-yuan Wang、Paul M. Keller、John A. Krawiec、Michael C. Jaye

  DOI：10.1016/j.bmcl.2008.11.033

  日期：2009.1

  Endothelial lipase (EL) activity has been implicated in HDL catabolism, vascular inflammation, and atherogenesis, and inhibitors are therefore expected to be useful for the treatment of cardiovascular disease. Sulfonylfuran urea 1 was identified in a high-throughput screening campaign as a potent and non-selective EL inhibitor. A lead optimization effort was undertaken to improve potency and selectivity, and modifications leading to improved LPL selectivity were identified. Radiolabeling studies were undertaken to establish the mechanism of action for these inhibitors, which were ultimately demonstrated to be irreversible inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.